After respondent (Piccadilly) declared bankruptcy under Chapter 11, but before its plan was submitted to the Bankruptcy Court, that court authorized Piccadilly to sell its assets, approved its settlement agreement with creditors, and granted it an exemption under 11 U. S. C. sec.1146(a), which provides a tax-stamp exemption for any asset transfer "under a plan confirmed under section 1129." After the sale, Piccadilly filed its Chapter 11 plan, but before the plan could be confirmed, petitioner Florida Department of Revenue (Florida) objected, arguing that the stamp taxes it had assessed on certain of the transferred assets fell outside sec.1146(a)'s exemption because the transfer had not been under a confirmed plan. The court granted Piccadilly summary judgment. The Eleventh Circuit affirmed, holding that sec.1146(a)'s exemption applies to preconfirmation transfers necessary to the consummation of a confirmed Chapter 11 plan, provided there is some nexus between such transfers and the plan; that sec.1146(a)'s text was ambiguous and should be interpreted consistent with the principle that a remedial statute should be construed liberally; and that this interpretation better accounted for the practicalities of Chapter 11 cases because a debtor may need to transfer assets to induce relevant parties to endorse a proposed plan's confirmation.

Held: Because sec.1146(a) affords a stamp-tax exemption only to transfers made pursuant to a Chapter 11 plan that has been confirmed, Piccadilly may not rely on that provision to avoid Florida's stamp taxes. The most natural reading of sec.1146(a)'s text, the provision's placement within the Bankruptcy Code, and applicable canons of statutory construction lead to this conclusion. Pp. 4-19.

(a) Florida's reading of sec.1146(a) is the most natural. Contending that the text unambiguously limits stamp-tax exemptions to postconfirmation transfers made under the authority of a confirmed plan, Florida argues that "plan confirmed" denotes a plan confirmed in the past, and that "under" should be read to mean "with the authorization of" or "inferior or subordinate" to its referent, here the confirmed plan, see Ardestani v. INS, 502 U. S. 129 . Piccadilly counters that the provision does not unambiguously impose a temporal requirement, contending that had Congress intended "plan confirmed" to mean "confirmed plan," it would have used that language, and that "under" is as easily read to mean "in accordance with." While both sides present credible interpretations, Florida's is the better one. Congress could have used more precise language and thus removed all ambiguity, but the two readings are not equally plausible. Piccadilly's interpretation places greater strain on the statutory text than Florida's simpler construction. And Piccadilly's emphasis on the distinction between "plan confirmed" and "confirmed plan" is unavailing because sec.1146(a) specifies not only that a transfer be "under a plan," but also that the plan be confirmed pursuant to sec.1129. Ultimately this Court need not decide whether sec.1146(a) is unambiguous on its face, for, based on the parties' other arguments, any ambiguity must be resolved in Florida's favor. Pp. 4-7.

(b) Even on the assumption that sec.1146(a)'s text is ambiguous, reading it in context with other relevant Code provisions reveals nothing justifying Piccadilly's claims that had Congress intended sec.1146(a) to apply exclusively to postconfirmation transfers, it would have made its intent plain with an express temporal limitation, and that "under" should be construed broadly to mean in "in accordance with." If statutory context suggests anything, it is that sec.1146(a) is inapplicable to preconfirmation transfers. The provision's placement in a subchapter entitled "POSTCONFIRMATION MATTERS" undermines Piccadilly's view that it extends to preconfirmation transfers. Piccadilly's textual and contextual arguments, even if fully accepted, would establish at most that the statutory language is ambiguous, not that the purported ambiguity should be resolved in Piccadilly's favor. Pp. 7-13.

(c) The federalism cannon articulated in California State Bd. of Equalization v. Sierra Summit, Inc., 490 U. S. 844 --that courts should "proceed carefully when asked to recognize an exemption from state taxation that Congress has not clearly expressed "--obliges the Court to construe sec.1146(a)'s exemption narrowly. Piccadilly's interpretation would require the Court to do exactly what the canon counsels against: recognize an exemption that Congress has not clearly expressed, namely, an exemption for preconfirmation transfers. The various substantive canons on which Piccadilly relies for its interpretation--most notably, that a remedial statute should be construed liberally--are inapposite in this case. Pp. 13-19.

484 F. 3d 1299, reversed and remanded.

Thomas, J., delivered the opinion of the Court, in which Roberts, C. J., and Scalia, Kennedy, Souter, Ginsburg, and Alito, JJ., joined. Breyer, J., filed a dissenting opinion, in which Stevens, J., joined.

Petitioner, a native and citizen of Nigeria, alleges that he married an American citizen in 1999. His wife filed an I-130 Petition for Alien Relative on his behalf that was denied in 2003. The Department of Homeland Security (DHS) charged Dada with being removable under the Immigration and Nationality Act for overstaying his temporary nonimmigrant visa. The Immigration Judge (IJ) denied the request for a continuance pending adjudication of a second I-130 petition, found Dada eligible for removal, and granted his request for voluntary departure under 8 U. S. C. sec.1229c(b). The Board of Immigration Appeals (BIA) affirmed and ordered Dada to depart within 30 days or suffer statutory penalties. Two days before the end of the 30-day period, Dada sought to withdraw his voluntary departure request and filed a motion to reopen removal proceedings under 8 U. S. C. sec.1229a(c)(7), contending that new and material evidence demonstrated a bona fide marriage and that his case should be continued until resolution of the second I-130 petition. After the voluntary departure period had expired, the BIA denied the request, reasoning that an alien who has been granted voluntary departure but does not depart in a timely fashion is statutorily barred from receiving adjustment of status. It did not consider Dada's request to withdraw his voluntary departure request. The Fifth Circuit affirmed.

Held: An alien must be permitted an opportunity to withdraw a motion for voluntary departure, provided the request is made before expiration of the departure period. Pp. 5-20.

(a) Resolution of this case turns on the interaction of two aspects of the Illegal Immigration Reform and Immigrant Responsibility Act of 1996--the alien's right to file a motion to reopen in removal proceedings and the rules governing voluntary departure. Pp. 5-12.

(1) Voluntary departure is discretionary relief that allows certain favored aliens to leave the country willingly. It benefits the Government by, e.g., expediting the departure process and avoiding deportation expenses, and benefits the alien by, e.g., facilitating readmission. To receive these benefits, the alien must depart timely. As relevant here, when voluntary departure is requested at the conclusion of removal proceedings, the departure period may not exceed 60 days. 8 U. S. C. sec.1229c(b)(2). Pp. 5-9.

(2) An alien is permitted to file one motion to reopen, sec.1229a(c)(7)(A), asking the BIA to change its decision because of newly discovered evidence or changed circumstances. The motion generally must be filed within 90 days of a final administrative removal order, sec.1229a(c)(7)(C)(1). Although neither the text of sec.1229c or sec.1229a(c)(7) nor the applicable legislative history indicates whether Congress intended for an alien granted voluntary departure to be permitted to pursue a motion to reopen, the statutory text plainly guarantees to each alien the right to file "one motion to reopen proceedings under this section," sec.1229a(c)(7)(A). Pp. 9-12.

(b) Section 1229c(b)(2) unambiguously states that the voluntary departure period "shall not be valid" for more than "60 days," but says nothing about the motion to reopen; and nothing in the statutes or past usage indicates that voluntary departure or motions to reopen cannot coexist. In reading a statute, the Court must not "look merely to a particular clause," but consider "in connection with it the whole statute." Kokoszka v. Belford, 417 U. S. 642 . Reading the Act as a whole, and considering the statutory scheme governing voluntary departure alongside sec.1229a(c)(7)(A)'s right to pursue "one motion to reopen," the Government's position that an alien who has agreed to voluntarily depart is not entitled to pursue a motion to reopen is unsustainable. It would render the statutory reopening right a nullity in most voluntary departure cases since it is foreseeable, and quite likely, that the voluntary departure time will expire long before the BIA decides a timely-filed motion to reopen. Absent tolling or some other remedial action by this Court, then, the alien who is granted voluntary departure but whose circumstances have changed in a manner cognizable by a motion to reopen is between Scylla and Charybdis: The alien either may leave the United States in accordance with the voluntary departure order, with the effect that the motion to reopen is deemed withdrawn, or may stay in the United States to pursue the case's reopening, risking expiration of the departure period and ineligibility for adjustment of status, the underlying relief sought. Because a motion to reopen is meant to ensure a proper and lawful disposition, this Court is reluctant to assume that the voluntary departure statute is designed to make reopening unavailable for the distinct class of deportable aliens most favored by the same law, when the statute's plain text reveals no such limitation. Pp. 12-16.

(c) It is thus necessary to read the Act to preserve the alien's right to pursue reopening while respecting the Government's interest in the voluntary departure arrangement's quid pro quo. There is no statutory authority for petitioner's proposal to automatically toll the voluntary departure period during the motion to reopen's pendency. Voluntary departure is an agreed-upon exchange of benefits, much like a settlement agreement. An alien who is permitted to stay past the departure date to wait out the motion to reopen's adjudication cannot then demand the full benefits of voluntary departure, for the Government's benefit--a prompt and costless departure--would be lost. It would also invite abuse by aliens who wish to stay in the country but whose cases are unlikely to be reopened. Absent a valid regulation otherwise, the appropriate way to reconcile the voluntary departure and motion to reopen provisions is to allow an alien to withdraw from the voluntary departure agreement. The Department of Justice, which has authority to adopt the relevant regulations, has made a preliminary determination that the Act permits an alien to withdraw a voluntary departure application before expiration of the departure period. Although not binding in the present case, this proposed interpretation "warrants respectful consideration." Wisconsin Dept. of Health and Family Servs. v. Blumer, 534 U. S. 473 . To safeguard the right to pursue a motion to reopen for voluntary departure recipients, the alien must be permitted to withdraw, unilaterally, a voluntary departure request before the departure period expires, without regard to the motion to reopen's underlying merits. The alien has the option either to abide by the voluntary departure's terms, and receive its agreed-upon benefits; or, alternatively, to forgo those benefits and remain in the country to pursue an administrative motion. An alien selecting the latter option gives up the possibility of readmission and becomes subject to the IJ's alternative order of removal. The alien may be removed by the DHS within 90 days, even if the motion to reopen has yet to be adjudicated. But the alien may request a stay of the removal order, and, though the BIA has discretion to deny a motion for a stay based on the merits of the motion to reopen, it may constitute an abuse of discretion for the BIA to deny a motion for stay where the motion states nonfrivolous grounds for reopening. Though this interpretation still confronts the alien with a hard choice, it avoids both the quixotic results of the Government's proposal and the elimination of benefits to the Government that would follow from petitioner's tolling rule. Pp. 16-20.

207 Fed. Appx. 425, reversed and remanded.

Kennedy, J., delivered the opinion of the Court, in which Stevens, Souter, Ginsburg, and Breyer, JJ., joined. Scalia, J., filed a dissenting opinion, in which Roberts, C. J., and Thomas, J., joined. Alito, J., filed a dissenting opinion.